JP5889342B2 - 触媒材料及び触媒材料を提供する方法 - Google Patents
触媒材料及び触媒材料を提供する方法 Download PDFInfo
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- JP5889342B2 JP5889342B2 JP2013557968A JP2013557968A JP5889342B2 JP 5889342 B2 JP5889342 B2 JP 5889342B2 JP 2013557968 A JP2013557968 A JP 2013557968A JP 2013557968 A JP2013557968 A JP 2013557968A JP 5889342 B2 JP5889342 B2 JP 5889342B2
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- 239000003054 catalyst Substances 0.000 title claims description 93
- 239000000463 material Substances 0.000 title claims description 85
- 238000000034 method Methods 0.000 title claims description 41
- 239000000243 solution Substances 0.000 claims description 101
- 239000012528 membrane Substances 0.000 claims description 85
- 229910052739 hydrogen Inorganic materials 0.000 claims description 45
- 239000001257 hydrogen Substances 0.000 claims description 45
- 238000006243 chemical reaction Methods 0.000 claims description 44
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 37
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 30
- 239000004372 Polyvinyl alcohol Substances 0.000 claims description 30
- 229920002451 polyvinyl alcohol Polymers 0.000 claims description 30
- 150000001875 compounds Chemical class 0.000 claims description 29
- 230000003197 catalytic effect Effects 0.000 claims description 27
- 229910052751 metal Inorganic materials 0.000 claims description 27
- 239000002184 metal Substances 0.000 claims description 27
- 239000002923 metal particle Substances 0.000 claims description 21
- 150000003839 salts Chemical class 0.000 claims description 19
- 238000005984 hydrogenation reaction Methods 0.000 claims description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
- -1 borohydride Substances 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 14
- 229920000620 organic polymer Polymers 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 10
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 10
- 229910052763 palladium Inorganic materials 0.000 claims description 9
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 7
- 229910052737 gold Inorganic materials 0.000 claims description 7
- 239000010931 gold Substances 0.000 claims description 7
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
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- 229910052703 rhodium Inorganic materials 0.000 claims description 6
- 239000010948 rhodium Substances 0.000 claims description 6
- 229910052707 ruthenium Inorganic materials 0.000 claims description 6
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- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims description 5
- 150000002576 ketones Chemical class 0.000 claims description 5
- 238000007254 oxidation reaction Methods 0.000 claims description 5
- 229910052697 platinum Inorganic materials 0.000 claims description 5
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 5
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- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
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- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
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- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 3
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- 229910017052 cobalt Inorganic materials 0.000 claims description 3
- 239000010941 cobalt Substances 0.000 claims description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 3
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- 238000006735 epoxidation reaction Methods 0.000 claims description 3
- 238000007037 hydroformylation reaction Methods 0.000 claims description 3
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052742 iron Inorganic materials 0.000 claims description 3
- 238000006317 isomerization reaction Methods 0.000 claims description 3
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- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 claims description 3
- 238000007082 phosphination reaction Methods 0.000 claims description 3
- 238000006884 silylation reaction Methods 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims 1
- 239000012670 alkaline solution Substances 0.000 claims 1
- 229910021529 ammonia Inorganic materials 0.000 claims 1
- 235000019253 formic acid Nutrition 0.000 claims 1
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 34
- 239000002243 precursor Substances 0.000 description 22
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- 238000002360 preparation method Methods 0.000 description 7
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- 150000001299 aldehydes Chemical class 0.000 description 6
- 238000005266 casting Methods 0.000 description 6
- ODEHKVYXWLXRRR-UHFFFAOYSA-N hex-3-yn-1-ol Chemical compound CCC#CCCO ODEHKVYXWLXRRR-UHFFFAOYSA-N 0.000 description 6
- 238000002354 inductively-coupled plasma atomic emission spectroscopy Methods 0.000 description 6
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- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 4
- 238000009396 hybridization Methods 0.000 description 4
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
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- SMWNFFKPVLVOQQ-UHFFFAOYSA-N methyl 2-acetamidoprop-2-enoate Chemical compound COC(=O)C(=C)NC(C)=O SMWNFFKPVLVOQQ-UHFFFAOYSA-N 0.000 description 3
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- 239000010935 stainless steel Substances 0.000 description 1
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- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
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- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
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JP7118971B2 (ja) | 2016-12-21 | 2022-08-16 | ビーエーエスエフ ソシエタス・ヨーロピア | 一軸押出機および一軸押出機の使用ならびに一軸押出機を用いて高吸収性ポリマの形態を変化させる方法 |
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WO2013121593A1 (en) | 2012-02-14 | 2013-08-22 | Nippon Kodoshi Corporation | Inorganic / polymeric hybrid catalytic materials with high activity in various solvents |
CN105061391B (zh) * | 2015-08-26 | 2017-09-01 | 潍坊医学院 | 一种芳炔基取代杂环酮类化合物的合成方法 |
CN105693498B (zh) * | 2016-03-21 | 2018-07-03 | 南开大学 | 使用甲酸和炔烃合成α,β–不饱和酸的方法 |
CN106513051A (zh) * | 2016-10-26 | 2017-03-22 | 上海纳米技术及应用国家工程研究中心有限公司 | 一种负载型可见光光催化剂及其制备方法 |
US10994263B2 (en) * | 2017-09-13 | 2021-05-04 | The University Of Akron | Polarized fiber mats for catalyst support structures |
JP2022512596A (ja) * | 2018-10-02 | 2022-02-07 | ビーエーエスエフ ソシエタス・ヨーロピア | 触媒粒子を含むフィルムの存在下で流体相で化学反応を実施するための方法 |
CN112742386B (zh) * | 2019-10-31 | 2022-08-12 | 中国石油化工股份有限公司 | 一种无机膜催化剂及其制备方法和应用 |
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JPH07171397A (ja) * | 1993-12-21 | 1995-07-11 | Nippon Oil Co Ltd | 固体酸触媒およびその製造方法 |
CN1230832C (zh) | 2001-10-30 | 2005-12-07 | 积水化学工业株式会社 | 质子传导性膜、其制造方法和使用其的燃料电池 |
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US7638459B2 (en) * | 2005-05-25 | 2009-12-29 | Uop Llc | Layered composition and processes for preparing and using the composition |
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JP5095249B2 (ja) * | 2007-03-28 | 2012-12-12 | ニッポン高度紙工業株式会社 | 高イオン伝導性固体電解質の製造方法 |
JP4871225B2 (ja) | 2007-07-02 | 2012-02-08 | ニッポン高度紙工業株式会社 | 高イオン伝導性固体電解質及びその製造方法並びに該固体電解質を使用した電気化学システム |
EP2222893B1 (en) * | 2007-10-19 | 2017-01-04 | Biointraface, Inc. | Coating method |
WO2009066079A2 (en) * | 2007-11-23 | 2009-05-28 | The University Court Of The University Of Dundee | Nano-particle dispersions |
KR101671845B1 (ko) * | 2010-03-31 | 2016-11-02 | 닛폰 고도시 코포레이션 | 유기/무기 혼성 촉매 물질, 그의 제조 방법, 그것을 수용한 선택적 공정 및 반응기에서의 용도 |
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JP7118971B2 (ja) | 2016-12-21 | 2022-08-16 | ビーエーエスエフ ソシエタス・ヨーロピア | 一軸押出機および一軸押出機の使用ならびに一軸押出機を用いて高吸収性ポリマの形態を変化させる方法 |
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US9527067B2 (en) | 2016-12-27 |
KR20140027201A (ko) | 2014-03-06 |
JP2014519964A (ja) | 2014-08-21 |
RU2014100970A (ru) | 2015-07-27 |
KR101773493B1 (ko) | 2017-08-31 |
EP2688668A1 (en) | 2014-01-29 |
CN103619479B (zh) | 2017-02-15 |
US20140128251A1 (en) | 2014-05-08 |
CA2832320A1 (en) | 2012-12-27 |
CN103619479A (zh) | 2014-03-05 |
WO2012176341A1 (en) | 2012-12-27 |
BR112013025999A2 (pt) | 2016-12-20 |
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